I think it will very much depend on your audience.
I'll personally not mention multisigs or HTLCs to my mum (most people don't care about this tech stuff, tbh), but I'll get her to download muun and demo a payment. Speed of transactions and low tx fees usually get people's attention. How deep you go down the rabbit hole with them will depend on their follow-up questions.
Also, i like using the analogy with mobile money (phone credit used for payment) as “off-chain” transactions, and transactions involving banks, as “on-chain” txs.
I used that analogy but people answer back with fair questions that are a answerable but are very subtle or technical to try to explain in a quick chat.
Like:
  • is it still decentralized and trustless? How?
  • why do we still need the base layer?
  • is lightning BTC the same as normal BTC?
  • why do I have to use a custodial wallet in LN? Oh you use a noncustodial LN? Why can't I do that as well? You need to run a node for that? But you don't need to do that in normal Bitcoin ... looks confused
I was opening that someone on SN would have gone through that and have a nice ELI5 explanation of the LN for those scenarios.
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Fair questions. I personally mostly speak to non tech people or curious nocoiners, so I get different questions.
I've read a very good eli5 explaination of the lightning, but unfortunately for you, the article was in french.
The first three chapters of A. Antanopoulos' Mastering Lightning are excellent and will answer most of these questions.
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Yes, can recommend Mastering Lightning! However, I have a background in computer science so I don't know if people with no such background will find it as easy to understand. But I think A. Antonopoulos does try to assume no previous knowledge.
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I found the first three chapters to be very accessible, but may be in just biased.
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